Overview A handsome entitled young man gets his heartbroken and after the usual cleanse in which he goes through a bunch of women, he finds one he wants to invest in. Thing is, is that feeling mutual? Characters Worth Noting Ray Livingston (Charles Brice) | Rochelle Marseilles (DeWanda Wise) | Paul (Alexander C. Mulzac) |…

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A handsome entitled young man gets his heartbroken and after the usual cleanse in which he goes through a bunch of women, he finds one he wants to invest in. Thing is, is that feeling mutual?

Characters Worth Noting
Ray Livingston (Charles Brice) | Rochelle Marseilles (DeWanda Wise) | Paul (Alexander C. Mulzac) | Jake (William Jackson Harper)

Main Storyline

When a man falls in love and has his heartbroken, does that excuse him from becoming a douchebag? When he becomes a guy who is “emotionally unavailable” but always willing to hook up and dish out half-hearted apologies, can him saying “I’m going through something” be an appropriate excuse? In many ways, Brice’s journey as Ray Livingston is about: How can a man, possibly, raised on this idea that doing certain things will win woman over get rejected?

Well, Rochelle Marseilles will give you your answer. This woman, one who is a prolific writer who does interviews in printed media and visual media, comes in contact with this little up and coming blogger through him harassing her on the street and following her. Despite this, though, she gives him one chance after another. Leaving you to question, at what point do you just look at someone and say never mind to their potential? When do you stop listening to their attempts to apologize and realize you just need to cut them off? That is, despite their sex game, despite them intriguing you, and despite them just having that something which leaves you wanting to leave an ellipsis on your relationship rather than just leave a single period ending what could have been?


After watching this movie, I have a few things on my mind. The first being how thankful I am for websites like Shadow and Act which help make movies like this get some type of press and then there was something said by Louis CK. In either his show or a comedy special, he notes how weird, and dangerous, it is that women still go out with men and that got me thinking.

We live in an age where social media brings people together and allows instant access to whatever someone is willing to put out there. Which, a lot of times, helps people connect, network, maybe even fall in love. But that is the ideal use of social media. On the other side of things, we have what Ray does. Ray uses social media to participate in hookup culture, to blog and perhaps heighten his ego with the idea someone cares what he thinks (which I know is so hypocritical of me to write), and he uses, once or twice, almost like a weapon since his blog is about dating and relationships.

So imagine watching a film like this, one which seems rooted in taking the concept of what makes an F— boy, a street harasser, and the man confused about what woman want, outside the bedroom, and puts it on film. That is what you get here. Ray is the type of guy who thinks there should be nothing wrong approaching a woman on a street, passive-aggressively trying to demand her attention, following her if he has to, and making her feel unsafe. Ray is the type who can’t be happy his friend found someone and instead refers to her as his sloppy seconds because they had a thing in the past. This is the kind of man Ray is.

On the other hand, you got Rochelle. Someone who is performed and written into a rare Black female lead who, in a multitude of ways, seems like a real person. She is more than just attractive, she is accomplished. Yet her decisions require a second thought. You are left wondering if her decisions are made to reestablish this is some kind of romantic movie or if they represent the complicated thought process that comes with dealing with a potentially threatening man like Ray.

Collected Quote(s)

I didn’t invent this, I merely participate.

—           How To Tell You’re A Douchebag

[…] I think some people come around for you to stick with and then others come around so that you can learn.

—           How To Tell You’re A Douchebag

TV Viewing


Perhaps the sole highlight is Rochelle. Granted, Ray does get a reaction out of me, which means Brice did his job as an actor, but Wise’s performance, and Rochelle’s decisions, are the only things which may keep this movie in my thoughts. To me, they represent the thing you question, and Louis CK mentioned in either his show or a comedy special: Why do women give men chances? Does it begin as a safety precaution, and they hope for the best? Is it truly just a belief that love exists, and this person might be the one? I mean, Rochelle’s thought process isn’t broken down, but in the grand scheme of things, she is one-half of a very familiar conversation worth analyzing.

Low Points

On the other hand, Ray doesn’t feel like he is worth a second thought. He, as many men don’t in the film, really present themselves as anything but different kinds of F— boys. Be it Ray who, even with how he became one, with nice guy entitles, never seemed that deep, or Paul, Rochelle’s boyfriend. Someone who seems to want an open relationship with Rochelle, for reasons you can’t understand why, especially when he wants to be in politics. Yet even with the open relationship bit, and him seeming kind of suspect, your thoughts remain with trying to understand Rochelle’s decisions and trying to figure out what women are willing to put up with to obtain certain needs, desires, or goals.

Lastly, when it comes to Ray’s friend Jake, honestly I was just left questioning if his sole purpose was to be that not all men are like Ray and Paul.

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